During the fifteenth century, the kingdom of Castile testified the production of an expressive number of travel reports to distant sites, travels which were carried out by members of the nobility, namely: the Embajada a Tamorlán, El Victorial, the work Andanzas y viajes de un hidalgo español e the Libro del infante Don Pedro de Portugal. Such records, given by the travelers who maintained relations with the House of Trastámara, have contributed in a decisive way to nourish the interest in traveling and knowing about other peoples and places, without, however, emphasizing the bad or good luck that could be faced among the paths. The risks and difficulties of the journeys deserved, therefore, special attention of the narrators, who suggested and described the cautions that should be taken to guarantee security and assistance to those who were traveling. Considering, as well, the conditions and value of travel in this period when the Iberian kingdoms were taking their first steps in search of expansion, this research aims to present and discuss the mentions of danger and assistance described by the nobles who were traveling to little-know places.